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N-bromobutanimide → HCID 10755030, compound

HRID 1532038
Notes
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Reaction equation

HRID 1532038 reaction equation
[CH2:1]([O:3][C:4]1[C:8]([CH3:9])=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:6][N:5]=1)[CH3:2].C1C(=O)N([Br:22])C(=O)C1>ClC(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:22][CH2:9][C:8]1[C:4]([O:3][CH2:1][CH3:2])=[N:5][O:6][C:7]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10845679HCID 10845679, compound

Product 1

HCID 10755030HCID 10755030, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Ethyl 3-Ethoxy-4-methylisoxazole-5-carboxylate (18 g, 91 mmol), NBS (17.5 g, 100 mmol), dibenzoyl peroxide (1 g, 4.1 mmol) in tetrachloromethane (500 mL) was boiled under reflux for 16 h. The mixture was cooled, filtered and concentrated in vacuo to afford the crude title compound (24.5 g, 97%).

Workup

  1. temperatureunder reflux for 16 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e01f0c340c884ad8bf0ba4c54b52957e
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06200999B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes